Sodium Hydroxide → 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 257040Notes

Reaction equation

HRID 257040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[N-:13]=[N+]=[N-].[Na+].[OH-].[Na+].C([O-])(O)=O.[Na+]>CS(O)(=O)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:13][CH2:7][CH2:6]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 787875-Methoxyindan-1-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

5-Methoxy-1-indanone 1 (30 g, 185 mmol) is dissolved in CH3SO3H (96 mL) and CH2Cl2 (100 mL), NaN3 (24 g, 370 mmol) is then added in portions over a 1/2 hour period. After 2 hours the reaction mixture is cooled to 0° and is subsequently neutralized with 5N NaOH solution (200 mL) and saturated NaHCO3 solution. The resulting mixture is extracted with EtOAc (3×200 mL). The combined organic phases are washed with saturated NaCl solution (3×200 mL), dried over Na2SO4 and concentrated in vacuo. The resulting brown solid is washed with hexanes (2×100 mL) to give 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline as a tan solid, m.p. 128°-130°.

Workup

  1. temperatureAfter 2 hours the reaction mixture is cooled to 0°
  2. extractionThe resulting mixture is extracted with EtOAc (3×200 mL)
  3. washThe combined organic phases are washed with saturated NaCl solution (3×200 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe resulting brown solid is washed with hexanes (2×100 mL)

Sources & evidence

ORD record
ord-86e846efa2d7497b9f7667075fc5b475
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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